tert-butyl 4-[(2S)-13-chloro-10-formyl-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-yl]piperazine-1-carboxylate | 403492-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并环庚烷吡啶
• 英文名称: tert-butyl 4-[(2S)-13-chloro-10-formyl-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-yl]piperazine-1-carboxylate
• CAS: 403492-74-0
• 化学式: C₂₄H₂₆ClN₃O₃
• 分子量: 439.942
• InChiKey: LQAXFWFBCGMLJB-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[(2S)-13-chloro-10-formyl-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-yl]piperazine-1-carboxylate 、 5-碘-1-甲基咪唑 在 乙基溴化镁 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 tert-butyl 4-[(2S)-13-chloro-10-[(S)-hydroxy-(3-methylimidazol-4-yl)methyl]-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-yl]piperazine-1-carboxylate 、 tert-butyl 4-{(11S)-8-chloro-6-[(R)-hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl}piperazine-1-carboxylate
  参考文献：
  名称：

  Discovery of C-imidazole azaheptapyridine FPT inhibitors

  摘要：

  The discovery of C-linked imidazole azaheptapyridine bridgehead FPT inhibitors is described. This novel class of compounds are sub nM FPT enzyme inhibitors with potent cellular inhibitory activities. This series also has reduced hERG activity versus previous N-linked imidazole series. X-ray of compound 10a bound to FTase revealed strong interaction between bridgehead imidazole 3N with catalytic zinc atom. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.12.013
• 作为产物：
  描述：

  Tert-butyl 4-[13-chloro-10-(hydroxymethyl)-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-yl]piperazine-1-carboxylate 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl 4-[(2S)-13-chloro-10-formyl-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-yl]piperazine-1-carboxylate 、
  参考文献：
  名称：

  Discovery of C-imidazole azaheptapyridine FPT inhibitors

  摘要：

  The discovery of C-linked imidazole azaheptapyridine bridgehead FPT inhibitors is described. This novel class of compounds are sub nM FPT enzyme inhibitors with potent cellular inhibitory activities. This series also has reduced hERG activity versus previous N-linked imidazole series. X-ray of compound 10a bound to FTase revealed strong interaction between bridgehead imidazole 3N with catalytic zinc atom. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.12.013

文献信息

• Novel farnesyl protein transferase inhibitors as antitumor agents
  申请人：——

  公开号：US20030229099A1

  公开（公告）日：2003-12-11

  Disclosed are novel tricyclic compounds represented by the formula (1.0): 1 or a pharmaceutically acceptable salt or solvate thereof. The compounds are useful for inhibiting farnesyl protein transferase. Also disclosed are pharmaceutical compositions comprising compounds of formula 1.0. Also disclosed are methods of treating cancer using the compounds of formula 1.0.

  揭示了由式（1.0）表示的新型三环化合物： 1 或其药学上可接受的盐或溶剂。这些化合物对抑制法尼基蛋白转移酶具有用处。还揭示了包括式1.0化合物的药物组合物。还揭示了使用式1.0化合物治疗癌症的方法。
• TRICYCLIC ANTITUMOR COMPOUNDS BEING FARNESYL PROTEIN TRANSFERASE INHIBITORS
  申请人：SCHERING CORPORATION

  公开号：EP1313725B1

  公开（公告）日：2007-04-11
• US7342016B2
  申请人：——

  公开号：US7342016B2

  公开（公告）日：2008-03-11
• Discovery of C-imidazole azaheptapyridine FPT inhibitors
  作者：Hugh Y. Zhu、Alan B. Cooper、Jagdish Desai、George Njoroge、Paul Kirschmeier、W. Robert Bishop、Corey Strickland、Alan Hruza、Ronald J. Doll、Viyyoor M. Girijavallabhan

  DOI：10.1016/j.bmcl.2009.12.013

  日期：2010.2

  The discovery of C-linked imidazole azaheptapyridine bridgehead FPT inhibitors is described. This novel class of compounds are sub nM FPT enzyme inhibitors with potent cellular inhibitory activities. This series also has reduced hERG activity versus previous N-linked imidazole series. X-ray of compound 10a bound to FTase revealed strong interaction between bridgehead imidazole 3N with catalytic zinc atom. (C) 2009 Published by Elsevier Ltd.